Diamond RingsGlam By Design

"Who wouldn't want to paint their face? It's the reason that kids go to the summer fair. You can become Batman or a Ninja Turtle. It allows you to embody this identity that is more than your constituent parts, it's this thing that takes over."

John O'Regan is an avid face painter. It's a relatively new hobby of his. Before he discovered it, he was known as the bespectacled vocalist/guitarist for Guelph, Ontario's toque-sporting post-punk outfit the D'Urbervilles. He's so towering and lanky he's impossible to miss in public ― especially with eye shadow streamed like a rainbow across his face. A self-proclaimed regular at the MAC store on Queen West in Toronto, removing his specs for some paint was an intrinsic part of becoming the solo project he's christened Diamond Rings.

"I'm not sure if it was a specific vision I had, but I had been working with [cousin] Lisa [Howard] and one night we decided to really go for something more overt and make a statement," he explains over coffee in the comfiest chair Starbucks has to offer. "It felt good to do and the response was really good. We continued and kept taking it further. I'm trained as a visual artist and have some sense of colour and a steady hand, so it's not too far out of my realm. Once I got used to it, it became like painting ― on your face."

As an art school graduate from University of Guelph, O'Regan, or Johnny O if you like, has placed as much emphasis on his flamboyant look as he has on his songs. Glamour is a major facet of his popular YouTube videos, record sleeves, press photos and stage show. Establishing this image was a deliberate effort to get himself seen and his music heard. "The kiss of death is an acoustic singer-songwriter, especially one who's a lead singer in a band," he says. "That's what you see so often."

In the summer of 2008, O'Regan was just coming off a tour with the D'Urbs, as they're affectionately known. While the tour was a success, something was off with the band's frontman. During some of the dates he was struck by an illness that came to a head during the band's North By Northeast performance. O'Regan began sweating and convulsing, and his bandmates rushed him to Toronto Western Hospital. There he was diagnosed with Crohn's disease, an inflammation of the digestive system that causes abdominal pain, vomiting, diarrhoea and weight loss. He required surgery and spent most of his summer in the hospital with an IV.

Where most people would be discouraged, O'Regan found inspiration. "I had three weeks in the hospital, so I thought let's try and make the best of this," he says. "It was the summer, fortunately. I could go outside dragging this IV pole around Kensington Market with my guitar [laughs]. I was really haggard looking. But by the end people would be coming into my room on their breaks and we'd do these über DIY shows. We'd pour some ginger ale and it was like a party. That would have been the first time I performed [first single] 'All Yr Songs' ― in the hospital, with the nursing staff, playing my keyboard and guitar. It's not a very glamorous beginning, but that's how I really started conceptualizing the project.

"It was kind of like I had my own subsidized artist residency," he continues. "I had this bed and a desk, and a guitar here, a crappy keyboard there. We couldn't bring a drum kit into the hospital, so the songs started taking on more of this singer-songwriter lyrical quality than what I had done previously. And that was it. I started writing songs just for me."

Even though all of the focus seems to be on Diamond Rings, O'Regan is still writing songs for the D'Urbervilles. The band he co-founded in Oshawa with Tim Bruton at the age of 18 are still kicking and prepping a second album slated for sometime next year ― once he's fulfilled his solo duties.

"The band's been really supportive. But I'm not gonna lie, it's made for some serious conflict of interest, having to sit down and make plans and decisions," he divulges. "I've been really lucky that they've allowed me the space to pursue the project for the last year, and fairly intensely. But it has made our work as a band better. I'm no longer trying to wedge these ideas that are now much better suited for my own music into this group dynamic. I'm more acutely aware of how I fit into that group than I've ever been. As the lead singer I'm often assumed to be the songwriter [and] lead idea generator, which is actually kind of the opposite for this new record. It's very much a band that doesn't have one leader, start to finish. Diamond Rings is a lot different, it's everything me."

For O'Regan, splitting his time between the two is also a satisfying experience, but he also feels that his two day jobs can scratch each other's back. "I'm believing sincerely that there will be a moment to bring the band back into the spotlight and I'm really excited about that," he says. "We played Pop Montreal [in October] and it was awesome. It's still fun to play rock music. And the other cool thing is that outside of Canada a lot of people aren't necessarily familiar with the band or aware that I have this other project. So it will be exciting to bring that to them. I think it's gonna work both ways. I'm gonna learn a lot over this next while that I'll use to help the band as well."

The transformation from John O'Regan of the D'Urbervilles to Diamond Rings was a shock for most, to say the least. His style is equal parts Bowie circa Aladdin Sane, Retro Junk and Foot Locker; his music borrows from Arthur Russell, Handsome Furs, Peaches and Grace Jones, and his embrace of the music video is as shrewd as Michael Jackson, Madonna and Lady Gaga before him ― albeit on a shoestring budget.

For most artists these days, music videos have become an afterthought mostly done for online promotion. Just over a year ago, the first Diamond Rings single "All Yr Songs" was released by O'Regan on the Hype Lighter label he founded with his roommate and video director Colin Medley. (A split with Kingston's PS I Love You, the single sold out almost immediately.) The video premiered on Pitchfork.TV and earned more than 100,000 views on YouTube. It was soon pulled from the site after Sony BMG mistook it for a video called "Diamond Rings" by UK rapper Chipmunk, who's signed to that label. The incident ended up as a headline story on music blogs, giving Diamond Rings unexpected exposure, ironically from having his music made unavailable. But O'Regan seems past the whole mix up, concluding, "It was essentially just some computer error on their part and some confusion over the name. The bummer is that we were promised Beyoncé records, which never arrived. You can print that."

After three more singles released in the last year, debut full-length Special Affections is brimming with confidence, yet sincere enough to separate it from the in-your-face haughtiness that contaminates most glam rockers. The listener is welcome to relate to O'Regan's self-examining words, move to his clapping R&B rhythms or repeat his hook-filled choruses. It works so well, you expect it to be a "big" sounding record devoid of flaws. But cutting his teeth in a DIY community, O'Regan opted to present his songs on the same modest level that launched the project.

"There were opportunities near the end to have some professional types come in to help mix, but I was a bit reticent to allow that at this stage," he says. "It's gonna grow, it's gonna get bigger and I would love a really polished pop album. I think ultimately though, the songs on the record are honest and earnest, but that's also how they sound. On one hand I feel fascinated with that world where you can make something so sonically airtight, it's almost a form of magic. But there's also something you can't beat about an artist like Arthur Russell, who worked on this level that was half homemade. For me it was trying to learn how to make drumbeats on GarageBand ― that was literally a big part of the record."

"How would it be the most fun to play a song?" is how he approaches compositions, which are all acoustic experiments at the core. "I don't ever want to be recording or putting something together and feeling as though that I'm not taking a bit of a risk. What Diamond Rings is about, essentially, is risk-taking."

O'Regan is the first person to tell you that he couldn't take any of these risks without a support system. He calls them his "team," which consists of cousin Lisa Howard, a professional make-up artist who helped him establish his look; roommate and co-owner of Hype Lighter, Colin Medley, along with partner Jared Raab who directed three of his music videos; and friend James Bunton of Ohbijou, who helped record Special Affections.

"It's not a democracy, in the traditional sense like some bands are, but they're there to help and knowing what's expected of them and what I need them for," he says. "There are certain things I can totally handle on my own and there are other things I've learned over time. Having grown up in a DIY community in Guelph, throwing and playing basement shows, making zines, I'm really fighting this urge to let go and give tasks to other people. But Diamond Rings has been a really big epiphany for me, where I've realized that sometimes there are people that are highly skilled in a specific area that can do what you need and do it better than you, provided that you give them the right direction.

"I've thought about this a lot, approaching this idea that music is my career and it still is a fun time, being able to sustain that kind of momentum and grow, develop and change, but do it in a way that doesn't really alienate the people that have been supportive so far. The best I can think of is to keep it honest… but also keep it consistently weird."

On any given day you'll find O'Regan decked out in animal print, spandex, oversized late '80s denim, a leather motorcycle jacket, fat Nike Air Force Ones and, of all things, a Nintendo Power Glove. And yet it's his undying and unlikely love for team sports apparel that is the most fascinating part of his personal style.

"Growing up, sports, bold colours, logos, that whole culture, everything was very defined and set out in this recognizable way. It's why I'll still go to a show and wear my Blue Jays cap," he says, fidgeting with that very hat. "To me, this says more about where I live, to an outsider, than any song. All of these images, the Toronto Blue Jays logo, the CN Tower, they speak to people."

Earlier this year, NME hailed O'Regan as an "ex-jock anti-hero." He laughs at the sensationalism behind the music tabloid's piece, but admits his interest in sports plays an important part in what he does.

"I was a jock in everything but attitude," he says. "When I think of this project, expressing this side of my personality has been a long time coming… I just never identified with that macho, homophobic culture, and to a large extent, that's what sports culture is. Music became kind of a refuge from that sports culture and environment. That's me realizing that I can embrace these two sides of myself."

So whether it's gold lamé leggings or a Raptors jersey, O'Regan says it all comes down to feeling good. "I like to pull from all these different sources, things I find interesting. It's something that I wouldn't do if I didn't really feel like it was something that made me feel good. And if you feel good you can project those feelings outwards to other people, which is what the show is about: touching people in a positive way."